Transition to Gentoo has been very smooth without any major issues. I like Gentoo. It is designed with developers and system admins in mind. The community is very much like Debian. If you patiently ask sensible questions on their IRC channel (freenode.net #gentoo) or post questions to their mailing list people answer them.
After compiling my entire system from scratch and setting up apache2, postfix mail, courier imap, samba 3.0 I have a very stable system. Let's see where my journey with Gentoo takes me. So far I am very happy!